Isomeric nonanols and decanols, their preparation, phthalic esters obtained therefrom and their use as plasticizers

Abstract

Mixtures of isomeric nonanols and decanols are obtained by joint aldol condensation of n-butanal and pentanals, and up to 1% by weight of 3-methylbutanal, hydrogenation of the aldol condensation product to the corresponding saturated alcohols, and separation from the reaction mixture of the components boiling at temperatures lower than those of the nonanols and decanols. The pentanals are mixtures of 60 to 90% by weight of n-pentanal and 10 to 40% by weight of 2-methylbutanal. The alcohol mixture is especially suitable for preparing ester plasticizers.

We claim:  
     
       1. A mixture consisting of isomeric nonanols and decanols which is the product of a joint aldol condensation of n-butanal and pentanals in a molar ratio of 1:2 to 1:1 
       wherein said pentanals comprise 60% to 90% by weight of n-pentanal, 10% to 40% by weight of 2-methyl butanal, and up to 1% by weight of 3-methyl butanal, to form an aldol condensation product,  
       hydrogenation of the said condensation product to form said isomeric nonanols and decanols, and separation therefrom of components having boiling points below those of said nonanols and decanols.  
     
     
       2. The mixture of  claim 1  wherein said pentanals comprise 65% to 80% by weight of n-pentanal, 20% to 35% by weight of 2-methylbutanal, and up to 1% by weight of 3-methylbutanal. 
     
     
       3. A process for preparation of a mixture consisting isomeric nonanols and decanols wherein the propylene and butenes are hydroformylated separately to form mixtures of butanals and pentanals, joint condensation of said mixtures in the presence of at least one basic catalyst to form a condensation product, 
       hydrogenation of said condensation product to form said mixture of said nonanols and decanols, and separation from said nonanols and decanols of components having boiling points below those of said nonanols and decanols.  
     
     
       4. The process of  claim 3  wherein said catalyst comprises rhodium-phosphine complexes. 
     
     
       5. The process of  claim 4  wherein said hydroformylation is carried out at 70° to 150° C. and under a pressure of 0.4 to 30 MPa. 
     
     
       6. The process of  claim 3  wherein said condensation is at 60° to 160° C. in the presence of at least one tertiary amine. 
     
     
       7. The process of  claim 3  wherein said hydrogenation is in the presence of at least one nickel catalyst at 100° to 180° C. under pressure of 1 to 10 MPa. 
     
     
       8. The process of  claim 3  wherein said separation is by distillation. 
     
     
       9. The process of  claim 8  wherein said distillation is at 100° to 125° C. under a pressure of 1 to 4 kPa. 
     
     
       10. A plasticizer which is the reaction product of the mixture of  claim 1  with phthalic acid and/or phthalic anhydride. 
     
     
       11. The plasticizer of  claim 10  wherein said pentanals comprise 65% to 80% by weight of n-pentanal, 20% to 35% by weight of 2-methylbutanal, and up to 1% by weight of 3-methylbutanal. 
     
     
       12. The process of  claim 3  wherein said mixture is esterified with phthalic acid and/or phthalic anhydride. 
     
     
       13. The process of  claim 12  wherein said catalyst comprises rhodium-phosphine complexes. 
     
     
       14. The process of  claim 13  wherein said hydroformylation is carried out at 70° to 150° C. and under a pressure of 0.4 to 30 MPa. 
     
     
       15. The process of  claim 12  wherein said condensation is at 60° to 160° C. in the presence of at least one tertiary amine. 
     
     
       16. The process of  claim 12  wherein said hydrogenation is in the presence of at least one nickel catalyst at 100° to 180° C. under pressure of 1 to 10 MPa. 
     
     
       17. The process of  claim 12  wherein said separation is by distillation. 
     
     
       18. The process of  claim 17  wherein said distillation is at 100° to 125° C. under a pressure of 1 to 4 kPa.